4-Bromophenol → HCID 57475643, compound

HRID 931550Notes

Reaction equation

HRID 931550 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.I[C:10]1[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].C([O-])([O-])=O.[Cs+].[Cs+]>CCOC(C)=O.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:10]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 10796Cesium carbonateHCID 26549Benzoic acid, 2,5-diiodo-

Product 1

HCID 57475643HCID 57475643, compoundYield 108%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateCatalystHCID 1140TolueneSolvent

Procedure

A RBF equipped with a reflux condenser was charged with 4-bromophenol (15.5 g, 89.4 mmol), 2,5-diiodobenzoic acid (25.700 g, 68.7 mmol), EtOAc (0.337 ml, 3.44 mmol), and toluene (100 mL). Cs2CO3 (44.8 g, 137 mmol) was carefully added portionwise. After stirring at RT for 1 min, the mixture was heated to 50° C. for 40 min and then heated to 100° C. for 20 hrs. The reaction mixture was allowed to cool to RT. The mixture was filtered through Celite and the solids were washed with EtOAc. The filtrate was diluted with water (200 mL), acidified with 2N HCl (300 mL), and extracted with EtOAc (4×500 mL). The organic extract was washed with brine and dried over sodium sulfate. The organic fraction was concentrated under reduced pressure to afford crude 2-(4-bromophenoxy)-5-iodobenzoic acid (31.1 g) as a tan oil that solidified upon standing.

Workup

  1. customA RBF equipped with a reflux condenser
  2. temperaturethe mixture was heated to 50° C. for 40 min
  3. temperatureheated to 100° C. for 20 hrs
  4. temperatureto cool to RT
  5. filtrationThe mixture was filtered through Celite
  6. washthe solids were washed with EtOAc
  7. additionThe filtrate was diluted with water (200 mL)
  8. extractionextracted with EtOAc (4×500 mL)
  9. extractionThe organic extract
  10. washwas washed with brine
  11. dry with materialdried over sodium sulfate
  12. concentrationThe organic fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2249ecc789124b79aeefae4725c6200d
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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